Family Trip to Jamaica Pt. 08


“Hi Jason, honey. Come here and let’s have a talk.” My mom gestured to the couch seat across from them. She was seated in between my father and my sister, each clad in a fluffy robe with, from what I could see, nothing underneath. They seemed completely relaxed squeezed together nearly in the buff on the couch.

The white of the robes brought out the beauty and brightness of both my sister and mother’s red hair. I couldn’t help think about how inviting they looked, until I noticed how flushed both my father and sister’s cheeks were. I was suddenly hit with flashes of memories of my father bending Lily over the hot tub, fucking her and slapping her ass. The sound of her screaming “Daddy” rang in my head.

I tensed up with emotions I could barely understand. My mother, intuitive as ever, spoke again. “Honey, I could see how upset you are at what you might have seen earlier. I think we all need to sit down and talk about what’s been going on.”

She was spot on, and there was a big part of me that agreed that all we needed to do was talk it out. But there was also a different part of me; angry, confused and jealous of my father. The inner conflict wouldn’t allow me to unclench and relax. I could offer no words that I felt would make them understand.

“Look son, I know you saw me and your sister earlier today…well…together,” my dad started awkwardly as he put his hand innocently on my sister’s knee.

I shifted uncomfortably in my seat. Lily chimed in this time.

“Jason, what’s wrong? It can’t have been that much of a shock. I mean, I know you’ve screwed mom. So what’s the big deal that I fucked dad?” She got right to the point and had none of the subtly of mom and dad.

“It’s not that,” I said. I owed it to them to pull myself out of this and try to say what I meant. “I guess it’s a little that. I just know it made me feel fucked up to see dad having his way with you.”

“Having his way with me?” Lily exclaimed, seeming offended. “I came on to him and was getting what I wanted.”

“Ugh, I didn’t mean to imply that. This whole trip has just been a lot, and I’ve loved everything I’ve experienced. I guess I was just jealous of dad and didn’t want to lose what I had with you.” Realizing something, I turned to mom, “or with you.”

Both my mom and Lily blushed and smiled slightly. “Oh, come here,” my mom said affectionately. She sat next to me and gave me a tight hug which felt warm and soothing. Of course, I could also feel her firm tits pressing into me which gave me the starts of stirrings in my loins. “We can sort this out, baby. Don’t worry.” She playfully stroked my leg and said “I don’t think any of us want to give up on anything we’ve gained on this trip.”

I looked up to see Lily and my Dad smiling at each other and to me. My mom stood up and went to the bar. “I think we all could use a drink to relax and sort through this. Lily come and help me.

Lily walked over to the bar to help my mom and I couldn’t help but smile in appreciation of the curve of her ample, soft breasts visible between the lapels of her robe. I was pulled out of my reverie by my dad coming to sit on the couch next to me. “Hey Jason, is it alright if I sit here?”

“Yea, of course,” I said. My words were casual but my tone was curt and unintentionally betrayed some lingering anger toward him.

“Listen kid. I’m sorry you had to walk in and see what you saw. At least without us all talking first. The days we’ve been here we haven’t really spent time together and it seems like we both have had some…life changing experiences.” I blushed and my anger thawed a little bit. “Lily even tells me you guys had a threesome with some girl from the beach for your first time.” I looked up at my dad, and he was smiling and looking impressed. It was clear he was trying to bond. It was working.

“Ha. Yea, I never thought my first time having sex would happen like that. And with my sister helping out no less.” Thinking about it now, this vacation had really pushed me at light speed through some sexual milestones. Losing my virginity, having a threesome, exploring my voyeuristic side. Not to mention discovering that I had a wellspring of sex living under the same roof as me this whole time. I wondered if this was what other people went through when they came here. Everyone was just so open.

“She’s a bit of a sexual wonder, isn’t she?” My dad and I both looked over admiringly at my sister. She and my mother were still preparing some blended drinks at the bar, working perfectly in sync. “She gets it from her mother. Your mom has always been quite adventurous when it comes to sexuality. She introduced me to our first threesome while we were still in high school!”

“Holy shit, I had no idea!” is all I could offer. I totally could believe it now after everything at the resort, but while growing up there was no way I’d match the picture of my perfect suburban mom with the seductress she turned out to actually be.

“Yup. Trust me, the games we get up to every time you and your sister bring home some of your hotter güvenilir bahis friends would make you blush.”

“Ha. From what they’ve told me, I think they would welcome being involved in whatever games you guys wanted to play,” I said, remembering all the times my friends talked openly about how they wanted to fuck my mother. Hell, my friend Tommy made no secret that he’d suck my dad off if given the chance.

My dad got a look on his face, “Hmmm, food for thought when we get home.” We laughed together at the likely half-joking thought of us drawing my and Lily’s friends into our new lifestyle. It felt good to joke with my dad.

“I’m sorry I freaked out. I’m not actually upset with you. But how did it first happen?” I asked, realizing I had clearly missed out on a lot to have missed my dad fucking my sister.

“It just sort of…happened naturally. Everyone at this resort is just so open and free with their impulses. It’s made me really be open and honest about stuff I’ve probably wanted for a long time.” My dad went on to tell me about the father and daughter he and my mom slept with and then the spa day with my sister. He already knew about my sister and I, so I filled him in on the details of me and Alex.

“Ha! So you competed with your mother and some young stud in a lap dance contest. And won! Honey, you left out some details,” my dad said, amused.

“Oops, did I,” my mom said, returning with our drinks. “I guess I don’t like to admit losing. It’s not my fault my partner couldn’t hold himself back from blowing a load right onto me.” As she said this she sat on my fathers knee, not bothering to adjust her robe which had fallen open to expose one pert breast. She gave my dad a little kiss of the lips, more tender than sexual.

Lily walked up with her own drink and interjected in her usual teasing way. “I’m starved and it seems like Jason’s feeling better from his little tantrum. Can we go get some food and call it a night?”

“Sounds good to me,” I said, hoping that things were ok with us if she was joking like that.

We all headed for the door when Lily made a quick spin to face me. “Lose the clothes, Jason. We aren’t covering up anymore.” I looked over her shoulder to see my parents were already placing their robes on hooks near the door. Lily herself was stripping hers off, giving me a full show of her silky smooth breasts and red capped labia.

“Your wish is my command, perv,” I said and stripped off my clothes, leaving them on a chair. Lily gave my cock a playful pull as we left to room to head towards the dining hall.

After a relatively normal, albeit naked, dinner, we headed back to our rooms and fell soundly asleep.


The next morning, I woke to the sensation of a mouth around my cock. I can’t begin to describe how delightful a way this is to wake up. Looking down with sleepy eyes, all I could see was a crop of red hair poking out from the sheet, bobbing slowly up and down. It struck me how strange and amazing it was that I couldn’t tell if it was my mom or my sister sucking my dick at the moment. What a life! Whoever she was, she was lovingly taking her time savoring the full length of my dick. I could feel the pressure of her tongue traveling up my shaft, then swirling around the head, making me moan with pleasure.

Hearing this, she moaned in response, making her mouth vibrate on me in an intensely pleasurable way. Her had reached up from under the sheet and caressed my bare chest. I placed my hand on her head, less as a guide but more as a point of contact to feel more connected to her. She responded by quickening her pace and grabbing my dick with one hand to jerk me while she sucked. Eventually the pleasure was too intense and I could hold back no longer. I shot rope after rope of cum right down her throat, and she accepted it gratefully, slowing down her stroking but applying more pressure. Whoever this was, she really wanted to milk me for all I was worth.

My entire body went limp and I lay there with eyes closed, breathing heavily. I could feel my companion shift in the bed and crawl up to lay next to me, running her hands along my body. Wrapped in my reverie, I didn’t bother look to see who it was but enjoyed the feeling of her body sliding against mine.

“Morning, little perv,” Lily spoke at last.

“Morning,” I said, still with my eyes closed. “That was a nice ‘good morning’ you just gave me.”

“I wanted you to start your day off right, especially after yesterday.” Ah, I see. This is her way to make sure I know she still wants me.

“Mmm. Well, you can be my alarm clock any day. Maybe I can return the favor?” I said as I caressed her perfect breasts and gave her nipple a pinch.

To my surprise, Lily shot up out of bed. “Oh no you don’t. If I don’t get up now, we are going to stay in bed the whole day. Not that that would be so bad,” she said with a smile. “I’m going to shower. You can join me after you see if mom and dad are awake.”

I watched her ass move as she made her way to shower, marveling at its türkçe bahis shape and jiggle.

As I passed through our joining door, I heard Lily start the shower. It made me want to rush so I didn’t miss a chance to jump in with her. Good things always happened when I showered with the girls in my family!

Mom and dad’s room was still dark, but I could make out their naked shapes on the bed. My mom lay on her side, making the shape of her ass stick out against her long slender body. My dad spooned against her, with one hand cradling her breast and his cock buried somewhere amongst her ass cheeks. Luckiest guy on Earth.

But who am I to complain with the way I just woke up.

Hearing my footsteps, my dad stirred and lifted his head. The movement woke my mother as well. “Morning, Jason.”

“Morning guys. Lily wanted me to get you up. I’m starting to think she just hates being the only one awake. She’s already in the shower.”

My mom smiled. “She’s always been an early riser. A shower sounds nice though. I’m going to hop in with her.” She stood up and gave a stretch, showing off the muscles in her body and giving me a eye full, causing my cock to stir. “Honey,” she said turning to my father, “Make sure you tell him about Michael’s message.”

I looked at my dad questioningly. It took him a second, but then he seemed to realize what my mom was talking about. “Oh yea. Michael is the guy I met at the pool the other day. The one who invited your mom and I over to…ummm… meet his daughter. He’s asked you and I to head off to his room after breakfast to help him with something for his daughter.”

“Help him with his daughter?” I sounded slightly annoyed. Was I supposed to be a tutor or something to the resort kids?

“I know, but he asked us to avoid cumming before going to the room, so I’m guessing it’s going to be something you’ll like,” my dad said smiling.

“Oh, well too late. Lily gave me a little wake up surprise this morning,” I said, laughing.

My dad smiled and looked down at my cock. “Well, you’re a young man. I’m sure you’ll be fine.” Then his smile broadened. “But what say you and I go see what your sister and mom are up to. Something tells me that watching them shower together will make sure we are worked up enough for whatever Michael wants from us.”

My dad and I made our way to my room’s shower and leaned against the sink to watch the show. My mother met our gaze with a smile as she liberally applied soap to Lily’s back. The site of them was intensely erotic. Both of their fair skin was turned a slight red from the heat of the shower, or perhaps the heat of each other. My mother knelt down to apply the soap sponge to my sister’s ass, making generous circles and taking great care to give them a playful squeeze. She drew her hands up her back, then down and around her waist to wash her stomach. As she did so, my mom pressed her tits against Lily’s back and their bodies seems to melt into each other. My mom took care to hold Lily close as she washed her beautiful tits.

My dad and watched in silence but both were hard as a rock. I instinctively brought my hand to my cock to start stroking but my dad stopped me. “Remember, we have to save it for Michael. Trust me, I’m aching too.” Looking down, I could see my dad’s cock was straining and looked ready for release, especially since he hadn’t already cum this morning as I had. His 8 inches stood firmly our over trimmed pubic hair. I realized we were the same size, and was strangely proud that I could measure up to my dad.

We watched Lily and my mom finish washing each other and exit the shower to towel off. Lily, pink with arousal and heat, looked over to see our hard cocks and asked mom, “Shouldn’t we help these two out?”

“No, sadly. They have to go after breakfast to help out a friend and his daughter. I want to hurry and eat too, so we can get to this spa you were raving about. That shower has me worked up and you promised me a good time there,” my mom said with a wink.


My dad and I left the room and got in the elevator headed to the top floor.

I couldn’t believe my eyes when we stepped into the room. Ours was nice, but this was palatial. Mike ushered us in.

“So glad you two could make it. Hi, Jason. Your dad has told me so much about you. By the looks of you,” he said as he scanned my naked body, it seems like you’ve really opened up to this place. I’m so glad you’re so comfortable.” Mike’s smile was genuine and warm. He seemed like the kindest and most gentle man. A naked Mr. Rogers.

“I’m starting to really enjoy being nude all the time. It’s a much more open way to live,” I replied.

“Open is the word,” Mike said, laughing. “Now, if you will follow me, the other gentlemen are already here and we can get started.”

Other gentleman? I looked to my dad, who was also a little confused. We walked over to the other side of the dining area to a room walled by windows overlooking the beach. The view was spectacular. Already in the room were two other men who I recognized güvenilir bahis siteleri from the resort. Charlie introduced himself first. He was about 6 feet tall, with tan skin, short black hair, an incredibly muscular build, and a cock that looked to be about 8 inches and thick without even being erect. He looked to be your typical jock type. Next to him was the young beach boy from the other day who had applied sunscreen on mom. He introduced himself as Aaron. Aaron looked to be in his teens, lean, with dark skin, a broad chest that wasn’t apparent when I saw him in uniform yesterday, and a decent sized dick of about 7 inches. He looked like he was semi hard already, probably from the same anticipation I felt as to what we were all doing here.

“Hey, I think we’ve met before, actually. On the beach.”

“Yea, we did. I served you and your mom,” Aaron gave a small laugh,” it was the highlight of my day.”

“Oh, she enjoyed it too, trust me.” I would only later think back to how strange it was to be shoot the shit with a guy about how great it was to feel up my mom.

Mike then joined us in the room. “Thank you all for coming. Last month, my daughter asked me for something I couldn’t give her just yet for her birthday. I’ve asked you to come here so you can help me fulfill her birthday wish. My little girl has been very good, so I promised her I would make it happen.” Mike spoke with such tenderness that it was clear he loved his daughter and would do anything for her.

He continued,” She wished to pleasure several men at once and have each of you cum on her to drench her. I think it’s sometimes called bukkake.” Each of us looked at each other with surprise, but also with clear excitement. My days had become so full of family fucking that I met this shocking wish from a young girl with glee and arousal. I looked over to my dad to see if I could detect any worry, but he just nodded to me and raised his eyebrows encouragingly. My dad had told me a little on the way over about his experience with Mike and his daughter before, but not much about her. The excitement stirred something in me, and I could feel myself getting hard. Looking around it was clear the other guys felt the same.

“Stephanie sweetie?” Mike called. Out of a bedroom on the other side of the suite, a short young girl made her way to our group. She was small, with a thin body, hair tied back in a ponytail, with tan skin, a hint of hips, and small handful sized breasts. Her eyes were large and her lips were red and full. She smiled at us and her braces gleamed in the light. She was dressed in a light silk robe and obviously had nothing else underneath, evident as her hard nipples pressed against the fabric. Everything about her made her seem innocent and young.

Stephanie looked around the room at the handful of nude men whose cocks were all full and waiting for her. We had naturally formed a semi-circle, and she took her place in front of us. Without a word passing between us, the men closed the circle, surrounding her. Stephanie spoke for the first time. “I’m so excited that you all want to make my wish come true.” She looked past us to her father. “Thank you for sharing, daddy.”

“I love you baby,” her father replied.

Stephanie then got on her knees and instructed us: “I want you guys to do whatever you need to do to cum. I’m open to everything, but please, whatever you do, don’t cum in me. I want every drop on my body.”

Aaron was the first to step forward, letting Stephanie take a hold of his cock and begin stroking it, using her two small hands to stroke his entire length. She wasted no time and after a few strokes, slid his head into her mouth and circled her tongue around the tip. Aaron moaned in pleasure. It was this moan that seemed to set everyone off as well. Each of us began stroking and acting on our desires.

Charlie positioned himself on the other side of Stephanie, and she, while still with Aaron in her mouth, reached out and began stroking his cock. Despite having Aaron’s dick in her mouth, Stephanie smiled and closed her eyes to enjoy her work. I stroked myself, feeling not ready to join in, instead choosing to enjoy watching her tight body. Out of the corner of my eye I saw my dad move forward.

He gave me a look as if to say “Here I go,” and got on his knees near Stephanie’s open pussy. I watched as my father gently rubbed the head of his throbbing cock along her slit, and Stephanie tensed and writhed in pleasure. The sight of it all was so sexy, I jerked myself harder.

“No need to take care of that yourself,” I heard our host say, suddenly realizing he was next to me, also stroking himself. “My girl can handle another young man, I’m sure,” he said, as he nudged me forward.

I stepped forward and Stephanie pulled Charlie’s dick out of her mouth to welcome me. “I’ve been waiting for you,” she said. Her desire for me made me feel like I grew an extra inch. She took hold of my cock and suddenly winced and moaned loudly. I looked down to see that my dad had taken that moment to push himself into her. As he moved in and out of her slowly, she groaned with pleasure and squeezed my cock as if to brace herself. Overtaken by the pleasure, she closed her eyes and hungrily took my penis fully into her mouth and began to suck me hard.

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